Plastics and process of producing the same



Pa sed has, 1939 s 2,142,145

PLASTICS AND PROCESS OF PRODUCING I THE SAME Joseph C. PatrickMon'isville, Pa., assign or to Thiokol Corporation, Yardville, N. 3., acorporation of Delaware No Drawing. Application October 6, 1937, SerialNo. 167,669

21 Claims. (Cl. 260-79) This invention relates to the production ofpersed form, inasmuch as under such conditions plastic or rubber-likebodies, having certain the high degree of dispersion of the polymervaluable and unique properties, and is acontinuapermits an extremelythorough removal of the tion in part of my co-pending application Ser.No. soluble impurities by washing. The difiiculty of 6 17,789, filedApril 23, 1935. transporting the latex in agglomerated form, and

The principles of the invention will be illusthe ease with which itsticks to parts of aptrated by the following specific and typicalexparatus, such as the stirrer, also makes it'adamples. It is intendedand will be understood visable to produce the polymer in the reactionthat the invention is illustrated by, but not limited vessel in itsdispersed latex-like form, from which 10 to, saidspeciijc examples. Theobject of the exvessel it can be readily removed because of its 10amples is to prdvide guide posts or markers to influid characteristics.If the polymer were prodicate the scope of the invention which will beduced in the reaction vessel in its coaguiated defined by the claimsultimately appended hereto: rubbery form it would be difficult to removeit Example 1.-l38 lbs. or 1 mol of dimercapto therefrom and it would becontaminated with the ethyl ether, SH.C2H4.O.C2H4.SH, are dissolved inreagents used in its manufacture. 15 100 gallons sodium hydroxidesolution containing Washing of the polymer in its dispersed condi- 90lbs. of NaOH; that is, an amount of NaOH tion may be accomplished in thereaction vessel slightly in excess of 2 mols. With this solution bystirring it up with successive quantities of there is intimately mixed afreshly prepared sust Settling and d a O the p ant pension of magnesiumhydroxide made by treating Wash q The Washing can, of course. e a0- 10pounds of MgClz.6HzO with 2 gallons of water complished in a d fi r v sn any nt. and adding thereto aso1utionof41bs.NaOH dist is desirable t ps v t polym in its solved in 0.5 gallon of water. h ti ixt r dispersedcondition until after removal, from the is then placed in a reactionvessel provided with reaction s stirring means and also means forheating, for The washed latex iS then transferred to 9. 25 example,steam coils. The mixture is subject d second vessel where coagulation oragglomeration to stirring and to this is gradually added an s p o ed byac fi o Sufficient ac d may oxidizing agent in the form of a solution ofsodium be added for t P pose until t e other liquid polysulfide (made,for example, by dissolving is acid to methyl Or 1' brought to a DH 0f348 lbs. or 2 mols of sodium tetrasulflde in 100 about 3. T e c a u atedp er s then dehy- 3 gallons of water) during a period of about tendrated by a y Suitable method, o milling. minutes. The reaction occursapproximately at mastication, kneadihg- In $11011 processes, roomtemperature and is somewhat exothermic. considerable heat is generatedWhich, t er The reaction is substantially completed after all With themechanical action, 0311588 he removal 01 the polysulfide has been added.The completion water. 35

of the reaction is indicated by withdrawing a In the above example,instead of sodium hysample, acidifying it and observing whether thedroxide as the agent for dissolving the diodor of mercaptan is absent.Stirring may be mercapto compound, other alkaline hydroxides continueduntil the reaction is completed as incould be used, for example,potassium, ammonium,

dicated by this test. lithium, calcium, barium, strontium, and in gen-40' The polysulfide acts as an oxidizing agent and eral any otheralkaline materials which will not converts the dimercapto ethyl etherinto a complex form highly insoluble sulfides. polymer or plastic. Theadvantage of the mag- Instead of magnesium hydroxide, other gelatnesiumhydroxide is that the said polymer or inous hydroxides may be employed,for example,

-15 plastic is produced in the form of a latex-like aluminum hydroxide,chromium hydroxide, liquid which has the unique property of being ferrichydroxide. Moreover, dispersing agents capable of intimate mixture withwater and other than hydroxides may be employed, for exsettling outsubsequently by the action of gravity. ample, gelatin, albumin, casein,agar, soluble This property permits intimate and thorough celluloseesters, etc.

washing to remove soluble impurities. Acidifica- Instead of sodiumpolysulfide, other poly- 50 tion of the latex-like liquid causes theseparation sulfides may be employed, e. g., potassium and of polymer asan agglomerated mass, the removal ammonium polysulfide or any othersoluble polyof the impurities from which would be a dimcult sulfide.Other oxidizing agents may be used, for problem. It is therefore highlydesirable to acexample, oxygen, air, ozone, hypohalites, andin complishthe washing while this mass is in disgeneral any oxidizing agenteffective in an a;

I alkaline solution, for example, hydrogen peroxide,

and metallic peroxides, perborates, chromates, dichromates, manganatesand permanganates, etc. The reaction is preferably carried on underalkaline conditions because it has been found that the reaction is veryfavorably influenced by such conditions.

Although in the above example, the step of agglomerating or coagulatingthe polymer was specifically described, it is in some cases advantageousto preserve the polymer in its dispersed form as such, e. g., for use incoating and impregnating various materials.

The product obtained in this case is a white coagulum which, upondrying, is, in thin sheets, a pale amber translucent and highly elasticsolid. When compounded with oxidizing agents including zinc oxide, itundergoes transformation by heat. The transformed product is highlyelastic and resistant to tear. It ispractically unaffected by immersionin gasoline over long periods and will withstand exposure to benzene. Itconfers a greatly enhanced resistance to natural and synthetic rubberssuch as chloroprene rubber and the polymerized butadienes, whencompounded with them, followed by curing of the mixture, in proportionsranging from 10% to 70% depending upon the degree of solvent resistancerequired. The presence of an organic acid or substance, as for example,an organic cyanide, capable of yielding small amounts of an organic acidat curing temperatures, in the presence of traces of moisture alwayspresent, greatly assists in the cure and enhances the final propertiesof the cured compound.

One of the important properties of the product of this invention is itscapacity to be transformed by heat into a plastic or product havingvaluable commercial properties.

The capacity of the polymer to be prepared in an intermediate form,amenable to many operations and uses, including removal of impurities,through drying, molding, spreading, coating, or dispersion in certainsolvents to produce cements while still retaining the capacity forsetting up or curing by heat to develop its ultimate properties, allcontribute to the commercial value of the process and product of thisinvention.

This property makes it possible to produce a highly purifiedintermediate polymer consisting substantially completely of an organiccompound free from inorganic electrolytes. While these impurities can beremoved satisfactorily from said intermediate polymer their removal fromthe final plastic would be diflicult.

Moreover, the wide variety of different products which may be made fromthe intermediate polymer make it possible to manufacture and sell thisintermediate form in bulk to different consumers who then may producetherefrom their particular product.

When the consumer gets his raw product it must be amenable to a widevariety of operations, such as molding, etc., while retaining thecapacity to change and develop its ultimate valuable properties at thewill of the consumer. Moreover, this change should not be accompanied byevolution of noxious or other gases or even a substantial evolution ofwater.

Therefore, while the preparation of the intermediate polymer as achemical factory operation may be accompanied by the production ofvarious by-products (removed by washing, etc.) the transformation fromintermediate to final polymer should be a reaction with as littleoutward manifestation as possible, except the development of valuableproperties, because while the preparation of the intermediate polymerfrom mercaptans occurs in a chemical factory equipped with means to carefor and remove undesired by-products, the transformation fromintermediate to final polymer occurs frequently in places where odors,etc., would make its use impractical.

Moreover, the change wrought by the consumer must be a simple one. Theproduction of the intermediate polymer requires a chemical reaction ofthe sort possible only in a chemical factory, whereas the curing ortransformation caused by the consumer is simple and requires only heat,e. g., heating in a mold.

For these and other reasons the present invention provides for thepreparation of an intermediate polymer, in a form capable of developingits valuable properties by a relatively simple subsequent operation, 1.e., mere heating.

The following is a specific illustrative example of the curing ortransformation of the intermediate polymer into its flnal state by heat.

Example 2 7 Pounds Intermediate polymer prepared as in Ex- Theseingredients are thoroughly mixed and thenrsubjected to a temperature of290 F. for minutes or 300 F. for 30 minutes.

The properties of the cured product are as follows:

- Tensile strength.About l700#/sq. in.

Elongation at brealc.About 500%. Temperature resistance.-Will not becomeinflexible above 45 F. Will stand about 200 F. continuously.

Solvent resistance-Substantially unaffected by water, gasoline, parafllnhydrocarbons, dilute acids and alkalies. Very slightly affected bysolvents such as benzol, toluol, xylol. Unailected by alcohol, acetoneand esters.

Tear and abrasion resistance-Excellent.

Electrical properties.Closely approaching those of natural rubber.

Stability.-Substantially unaffected by age or sunlight. Uniquelyresistant to ozone, oxygen or air Efiect of gases.Highly resistant todiffusion. About 40 times less permeable than natural rubber.

The mechanism of polymer formation consists in the removal of H-atomsfrom mercaptan terminals by oxidation thus:

where oxygen or an oxygen-yielding oxidizing agent is used. The dimerthus formed again reacts with oxygen to form a tetramer. This thenreacts to form an octomer and finally a long chain polymer results withmercaptan or mercaptide terminals. Thus, when the reaction is carriedout in a sodium hydroxide solution the polymer has the formulaN83.R.S.S.R.S.S R.S.S.R.SNa

In this condition the polymer remains in a highly dispersed form inalkaline solution in the presence of a dispersing agent and can bewashed free of impurities, prior to coagulation. Owing to this property,the thoroughly washed dispersion or latex yields a coagulum free fromwater soluble impurities and electrolytes, which if allowed to remainwould impair its useful properties.

Upon acidification, the dispersion is coagulated and the polymerseparates as a rubber-like plastic mass. In that condition the metallicterminals are converted into hydrogen and the polymer has the formulaHS.R.S.S.R.S.S R.S.S.R.SH

Owing in part at least to the remaining or residual activity of saidhydrogen terminals the polymer is potentially reactive and undergoes afurther change upon heating with oxidizing agents. By this change itsphysical properties are greatly improved. Its valuable and uniqueproperties become developed by this further change.

In its intermediate stage the polymer may be mixed with various fillersand oxidizing agents and subsequently molded into any desired final formunder heat and pressure.

In general, it has been found that this invention can be carried out asdescribed by oxidizing compounds containing an --SH group attached toeach of two different carbon atoms and a long list of reactions isherewith submitted in support of this statement.

There are certain properties common to all. such compounds. First, as tothe uncured polymer, it is more or less plastic and can be compoundedwith various materials including oxidizing agents. Upon heating withoxidizing agents, e. g., zinc oxide and other metallic and non-metallicoxides or organic oxidizing agents, e. g., benzoyl peroxide andpolynitro-aromatic compounds, a curing reaction takes place exemplifiedin Example 2. The uncured polymer has the ability to combine with sulfurat moderate temperatures, e. g., to F. and to yield a reaction productfrom which said sulfur is given off in nascent condition at highertemperatures, especially in the presence of a substance which willcombine with said sulfur such as natural and synthetic rubbers,unsaturated glycerides and fatty acids, etc. The potentially reactive orintermediate polymer of this invention is a long chain compound havingorganic radicals linked together by a disulfide group -'S.S thusHS.R.S.S.R.S.S.R.SS R.SS.R.SH

HS.R.SS R.SH+2S=HS.R.fi.fi

R.SH

The added sulfur is in a labile condition.

The tetrasulfide having this labile sulfur available is an excellentvulcanizing agent for natural and synthetic rubbers, the vulcanizedproduct being free from sulfur bloom and this is especially valuable inthe case of butadiene polymers which bloom rather badly when vulcanizedwith free sulfur.

Secondly, as to the common properties of the cured polymers. They areall characterized by toughness and more or less elasticity, uniqueresistance to solvents for rubber, unique stability against oxygen, air,sunlight and water.

, However, the properties of the atomic structure to which is joined thecarbon atoms connected to said SH groups influences the properties ofthe polymer produced by oxidation and certain classes of said structurehave been found to confer remarkable properties on said polymer.

One of these classes is that characterized by I saturated straight chaincarbon atoms for example:

riswm) 2SH Dimercaptoethane.

HS(CH2) 38H Dimercapto propane.

HS CH2 5SH Dimercapto pentane. HS(CH2)10SH Dimercapto decane.

Another class is that characterized by unsaturated carbon atoms. Forexample:

,HS.CH2CH=CH.CH2.SH 1,4 dimercapto butene 2,3.

Another class is that characterized by ether lHS.CH20.CHz.C.CHzO.CH2.SH- -2,2 dimethyl-l,3 di (mercapto methoxy)propane.

Another class is that characterized by aryl groups. For example:

HS.CH2C6H4.CH2SH p,p' dimercapto xylene. HS.C2H4.0-C6H4.0C2H4SH Mdimercapto diethoxy benzene.

It will be noted that the latter compound is also characterized by etherlinkages.

A. Where the carbon atoms to which the SH groups are attached are joinedto and separated by straight-chain saturated carbon atoms (methylene andpolymethylene groups).

Examples 3 to 6 below set forth certain specific polymers produced byoxidizing members of the class mentioned.

Example 3.l mol. of any of the following products is treated as inExample 1.

(a) srucmnsu 94 pounds. (1)) SH.(CH2)3SH 108 pounds. (0) SH.(CH2)4SH 122pounds. (d) SH.(CH2)5SH 136 pounds. (e) SH.(CH2)6SH 150 pounds. (I)SH.(CHz)mSH 206 pounds. (g) jsmcnmosn 346 pounds.

These polymers show a decreasing degree of flexibility as the length ofthe carbon chain decreases.

For example: a to c are moldable powders, d to j inclusive aredefinitely elastic solids, and g is a tough leathery polymer.

Example 4.--2,3 dimercapto butane CH:4.CH.CH.CH:

SH H

122 pounds are treated as in Example 1.

It gave a soft elastic polymer substantiallyodorless both before andafter cure.

All of the above polymers are intermediate products produced as inExample 1 and were then compounded and cured by heating as in Example 2.The properties mentioned below re fer to the properties after curing.

The products of Examples 3(a), 3(b) and 3(0) are characterized byextreme hardness, e. g. over 100 on the Shore durometer, low elongationless than 100%, high tensile strength as high as 3000 pounds per squareinch, extreme stability against solvents and chemicals.

As the length of the carbon chain increases, e. g., Examples 3(d) to3(a) inclusive, the hardness, tensile strength and resistance tosolvents and chemicals decreases, flexibility increases.

Examples 4 and 5 differ from Example 3, in that in the latter the SHgroups are attached to terminal primary carbon atoms whereas in theformer the SH groups are attached .0 secondary carbon atoms and it is tobe noted that the products of Examples 4 and 5 are more elastic thanthose of 3(0) and 3(b). The product of Example 6 is similar to that ofExample 4.

B. In this class the carbon atoms to which the SH groups are attached,are joined to and separated by branched chain saturated carbon atoms.

Examples of this class are set forth below:

1 H S.CII;CH.CH:SH

1,3 dimercapto isobutane (H S .CH:O),CH(|J OH,

OH; 1,3 di 09,5 mercopto methoxy) 2,2 dimethyl propane H S .011. CH: S H

Propylene dimercaptan 136 pounds are treated as in Example 1.

The characteristics of this polymer are, in the main, similar to thoseof the polymer described under Example 7. It is somewhat lessrubber-like but is tougher and harder.

In general the uncured and cured polymers of this class display greatersoftness and elasticity than those produced from the correspondingsaturated straight chain compounds.

C. Where the carbon atoms to which the SH groups are attached are joinedto and separated by atomic structures characterized by an ether or thioether linkage.

Example 9.-Di mercapto ethoxy ethyl ether 182 pounds or 1 mol isdissolved in an alkaline solution and treated as in Example 1 above.

The product obtained was a greyish white mass. It has highly elasticproperties and prior to curing thin strips of the material, submitted toX-ray examination, exhibit a fiber diagram on stretch similar to thatgiven by natural rubber. The product is practically odorless.

Example 10.-Di (mercapto methyl) ether SH.CH2.O.CH2.SH

110 pounds or 1 mol is treated as in Example 1 above.

The uncured product is, when dried, a pale amber elastic mass. Aftercuring it is a tough rubber-like solid, highly resistant to the actionof 'most organic solvents and even withstands, to a considerable degree,the action of chlorinated solvents.

Example 11.--Di mercapto thio ethyl ether 154 pounds or 1 mol is treatedas in Example 1 above.

The uncured product is, when dried, a pale yellowish tough and somewhatelastic mass. After curing its resistance to water absorption is higherthan that of the product produced from the corresponding ether compound.

Example 12.-Di mercapto methyl ethyl ether 196 pounds or 1 mol istreated as in Example 1. Example 14.Di (mercapto methyl) thio etherSH.CH2.S.CH2.SH

126 pounds or 1 mol is treated as in Example 1. This product is, ingeneral, quite similar to the product described in Example 12. Aftercuring it is entirely non-permeable to water or dilute saltsolutions,'even after long exposure.

Example 15.-Di (gamma, mercapto propyl) formal,

SH.CH2.CH2.CH:.O.CH2.O.CH2.CH2.CH2.SH

196 pounds of 1 mol is treated as in Example 1.

Example 17.1 mercapto methoxy, 2 methoxy,

2 mercapto ethane.

154 pounds are treated as in Example 1.

When dry it is a pale amber odorless polymer, elastic and quite tough.

Example 18.-Para' di (beta mercapto ethoxy) I benzene 230 pounds aretreated as in Example 1.

- The polymer is a tough, pliable, somewhat elastic mass. It graduallyturns from gray to amber on standing.

When one empirical molecular weight, 228 g.

of the polymer, is compounded with 2 gram atoms of sulfur, 64 g., acombination occurs presumably to form a coordinated compound with thesulfur.

in S-S-CQHQ-OOO-CIHl-S-S- This sulfur cannot be extracted with ordinarysulfur solvents, such as acetone, in the cold. However, when from 5 to10% of the polymer are compounded into a rubber stock containing nosulfur, a good tight cure of the rubber is obtained and nobloom isencountered, even on lon exposure of the rubber stock. This provides afeasible method of rubber cure without free sulfur, and the, fact thatthe cure is surprisingly tight would tend to indicate that the excesssulfur is still combined with the polymer, only such sulfur as canactually be combined with the rubber phase having been given up.

This aryl-oxygen linkage possesses marked negative characteristics andconfers increased reactivity upon the SH groups.

Example 19.--Di (mercapto methoxy) ethane SH.CH2.O.CH2.CH2.O.CH2SH 154pounds are treated as in Example 1.

The product obtained'is a white material capable of being molded underheat and pressure, upon which it becomes tough and elastic.

Example 20.--Di (gamma mercapto propyl) sulfideSHCHs.CH2.CH2.S.CH2.CH2.CH2.SH

.182 grams are treated as in Example 1.

The polymer is a white granular powder capable of being molded underheat and pressure. After forming, the product is tough and elastic. Whencompounded with two or three gram atoms of sulfur per unit mol of thepolymer and heated to 100 C. for from 3 to 4 hours, it becomes a soft,elastic, rubbery mass.

In general, the outstanding characteristic of cured plastics producedfrom class C compounds, as distinguished from class A and B compounds,isresistance to low temperatures without becoming brittle. There was noway of preqmting this unique property and it is wholly unexpected. Thisproperty is combined with resistance to solvents comparable to thecompounds of class A and elasticity and elongation superior thereto.

All of the compounds of class C have an ether or thio ether linkagebetween the carbon atoms to which the-SH groups are attached and to thisstructure is attributed the special and out standing properties ofpolymers and plastics from Example 3(a) Example 9 Tom rature at whichmato: al loses flexibility -l0 F. F. e strength. 1000 lbs/sq. in. 2000lbs. sq. in, Elongation at break 200% 500% Permanent set or deformationalter elongation 40% 10% In addition to the examples of COLIIDOUlldShaving an ether linkage set forth above, the following are alsosubmitted.

Example 21.'-p, p dimercapto ethyl carbonate 1 mol is treated as inExample. 1.

Example 22.Gamma, gamma dimercapto propyl carbonate 1 mol is treated asin Example 1.

Example 23.-Gamma, gamma dimercapto propyl etherSH.CH2.CH2.CH2.O.CH2.CH2.CH2.SH

1 mol was treated as in Example 1.

The compounds of Examples 21 and 22 have between the carbon atoms towhich the -SH groups are attached, a structure combining thecharacteristics of an ether, a ketone and an ester.

D. Where the carbon atoms to which the SH groups are attached are joinedto-and separated by structures characterized by the presence ofunsaturated carbon atoms.

Example 24.-1,4 dimercapto, 2,3 butene HS.CH2.CH=CH.CH2.SH

120 pounds are treated as in Example 1.

The polymer is a rubbery spongy mass. When compounded with sulfur andzinc oxide and heated becomes a highly elastic rubbery solid.

Example 25.-1 mercapto, 3 mercapto tolyl, 2,3 propene,

196 pounds were treated as in Example 1.

' The properties of this derivative are quite similar to those describedunder Example 24. The presence of the double bond is more of adeterminant of the properties of the polymer than the benzene ring.

The polymers produced as in Examples 24 and '25 are greyish-white massespossessing mar d Said marked resiliency is associated with the fact thatthe carbon atoms to which an -SH group is attached are separated bystructures including unsaturated carbon atoms. This structure possessesmarked negative properties and confers reactivity upon the SH groups.

There is a property common to the compounds used in classes 0 and D. InC the structure separating the carbon atoms to which the -SH groups areattached is characterized by ether or thio ether linkages. Theselinkages are markedly negative in character and this negative propertyconfers reactivity on the -SH groups and the carbon atoms to which theyare attached.

The presence of structures characterized by unsaturated carbon atoms asexemplified above in Examples 24 and 25 confers properties on thepolymer made therefrom similar to those possessed by polymers made fromthe di-substituted ethers and thio ethers; and those propertiesincluding the ability to withstand low temperatures without losingflexibility will be found described above.

The polymers of class C and D can all be cured as in Example 2.

E. Where the carbon atoms to which the 8H groups are attached are joinedto and separated by an aryl group or groups.

Example 26.-Para di mercapto xylene SH.CHOCH:.SH

170 pounds are treated as in Example 1.

The product is a yellowish powder with a faint pleasant aromatic odor.It can be molded with heat and pressure. It combines with sulfur to givea tough elastic solid.

Example 27--Para di mercapto benzene sir 226 pounds are treated as inExample 1.

Polymer is an elastic solid very slightly soluble in benzene butinsoluble in alcohol and ether.

The polymers of this group E can all be cured as in Example 2. Theuncured polymers of group E have a tendency to be granular.thermoplastic powders in contrast to the elasticity of the polymers madefrom compounds when the -SH groups are separated by ether or a thioether linkage and unsaturated carbon atoms (groups C and D). Thepolymers of group E acquire elasticity upon curing.

In general, the polymers produced can be classified as follows as toproperties:

Groups C and D. Elasticity combined with property of retaining thischaracteristic at low temperatures (after curing).

Group E. Granular condition of uncured polymer. Cured polymer hard withhowever substantial elasticity.

Groups A and B. These fall between those of E on the onehand and C and Don the other hand.

Thus, where the SH groups are attached to classes of groups havingcertain common properties, e. g., (A) saturated straight-chainhydrocarbons, (B) saturated branched hydrocarbons, (C) ether and thioether linkage, (D) unsaturated carbon atoms, (E) aryl groups, theproperties of the resulting polymer are different and those differenceshave been pointed out.

I can therefore build up compounds having the I predominatingcharacteristics of groups A to E respectively. Moreover I can buildstructures combining the characteristics of these groups or any of them.This I can do by selecting a compound having the following formula:

where R, R1 and R: represent diiferent classes from the group consistingof ether linkages, aryl groups and saturated hydrocarbons, for example.When such a compound is oxidized as in the present invention, and theresulting polymer cured, it will partake the advantages characteristicof these different classes. This fusion of properties is illustrated inseveral of the polymers specifically mentioned above.

Another manner in which I can fuse into one polymer the advantageousproperties derived from the use of different atomic structure is toselect compounds having the formulas HS.R.SH and SHBl-SH and treat amixture of these compounds with an oxidizing agent so as to cause thefollowing reaction R and R1 being members from diflereut classes ofcompounds. A specific example of this procedure is as follows:

Example 29.2 mols or 276 pounds of dimercapto ethyl ether and 1 mol or94 pounds of dimercapto ethane HS.C:H4SH are treated as in Example 1,except that the caustic soda, magnesium chloride and other reagents areused in the three fold molecular ratio.

I claim:

1. The process which comprises providing an organic compound having an-SH group attached to each of two different carbon atoms, dissolvingsaid compound in an alkaline solution and subjecting said solution to anoxidizing treatment to convert said compound into a polymer andseparating said polymer from said solution in a form capable of beingcured by a subsequent heat treatment.

2. The process which comprises providing an organic compound having an--SI-I group attached to each of two terminal carbon atoms, dissolvingsaidcompound in an alkaline solution and subjecting said solution to anoxidizing treatment to convert said compound into a polymer andseparating said polymer from said solution in a form capable of beingcured by a subsequent heat treatment.

3. The process which comprises providing an organic compound having anSH group attached to each of two different carbon atoms, oxidizing saidcompound in a disperson medium and obtaining a polymer in dispersedform, separating the polymer from said medium and from impurities, andobtaining the polymer in intermediate potentially reactive form capableof being cured by a subsequent heat treatment.-

4. The process which comprises providing an organic compound having anSH group attached to each of two terminal carbon atoms, oxidizing saidcompound in a dispersion medium and obtaining a polymer in dispersedform, separating the polymer from said medium and from impurities, andobtaining the polymer in intermediate, potentially reactive form capableof being cured by a subsequent heat treatment.

5. The process which comprises providing an organic compound having anSH group attached to each of two different carbon atoms, dissolving saidcompound in an alkaline solution and subjecting said solution to anoxidizing treatment in the presence of a dispersing agent and therebyconverting said compound into a polymer in the form of a latex-likedispersion capable of being washed with water, washing said dispersionto remove impurities, and coagulating the polymer from said washeddispersion in the form of a potentially reactive mass capable of beingcured by heat.

6. The process which comprises providing an organic compound having anSH group attached to each of two different carbon atoms, dissolving saidcompound in an alkaline solution and subjecting said solution to anoxidizing treatment in the presence of a dispersing agent to convertsaid compound into a polymer in the form of a latex-like dispersionthereof, acidifying said dispersion and separating said polymer in theform of a potentially reactive mass capable of being cured by heat.

'7. The process of producing a polymer capable of producing a syntheticproduct highly resistant to ordinary solvents, and mechanical andelectrical stresses which comprises subjecting an organic compoundhaving an SH group attached to each of two diiferent carbon atoms tooxidation in a dispersion medium and obtaining a polymer in the form ofa dispersion, removing impurities from the dispersion and separating thepolymer therefrom as an intermediate potentially reactive mass capableof being compounded with various fillers and oxidizing agents andundergoing a transformation under the influence of heat and saidoxidizing agents into a synthetic product having the properties firstmentioned above.

8. The process which comprises providing an organic compound having anSH group attached to each of two different carbon atoms which atoms arejoined to and separated by a structure selected from the groupconsisting of ether and thio ether linkages, oxidizing said compound andconverting it into a polymer.

9. The process which comprises providing an organic-compound having anSH group attached to each of two terminal carbon atoms which atoms arejoined to and separated by a structure selected from the groupconsisting of ether and thio ether linkages, oxidizing said compound andconverting it into a polymer.

10. The process which comprises providing an organic compound having anSH group attached to each of two different carbon atoms which carbonatoms are joined to and separated by an ether linkage, oxidizing saidcompound and converting it into apolymer. 11. The process whichcomprises providing an organic compound having an SH group attached toeach of two terminal carbon atoms which carbon atoms are joined to andseparated by an ether linkage, oxidizing said compound and converting itinto a polymer.

12. The process which comprises providing an organic compound having anSH group attached to each of two different carbon atoms which carbonatoms are joined to and separated by a structure including unsaturatedcarbon atoms, oxidizing said compound and converting it into a polymer.

13. The process which comprises providing an organic compound having anSH group attached to each of two terminal carbon atoms which carbonatoms are joined to and separated by a structure including unsaturatedcarbon atoms, oxidizing said compound and converting it into a polymer.i

14. The process which comprises providing an organic compound having anSH group attached to each of two different carbon atoms which atoms arejoined to and separated by a structure including an aryl group,oxidizing said compound and converting it into a polymer.

15. The process which comprises providing an organic compound having anSH group attached to each of two terminal carbon atoms which atoms arejoined to and separated by a structure including an aryl group,oxidizing said compound and converting it into a polymer.

16. The process of producing rubber-like plastics which comprisesproviding a mercaptan having one SH group attached to each of the twoterminal carbon atoms, dissolving said compound in an alkaline solution,subjecting said solution to an oxidizing treatment in the presence of adispersing agent to convert said compound into a polymer in the form ofa latex-like dispersion thereof, acidifying said dispersion andseparating said polymer in the form of a potentially reactive masscapable of being cured by heat.

17. The process of producing rubber-like plastics which comprisesproviding a mercaptan having one SH group attached to each of the twoterminal carbon atoms, dissolving said compound in an alkaline solution,subjecting said solution to an oxidizing treatment in the presence of adispersing agent to convert saidv compound into a polymer in the form ofa latex-like dispersion thereof and separating the polymer from saiddispersion in the form of a potentially reactive mass capable of beingcured by heat.

18. The process of producing rubber-like plastics which comprisesproviding a mercaptan having one SH group attached to each of the twoterminal carbon atoms, dissolving said compound in an alkaline solution,subjecting said solution to an oxidizing treatment in the presence of adispersing agent to convert said compound into a polymer in the form ofa latex-like dispersion thereof, washing said dispersion to remove impurities therefrom and coagulating the polymer from said dispersion inthe form of a potentially reactive mass capable of being cured by heat.

19. The process which comprises providing a mercaptan compound havingone SH group attached to each of the two terminal carbon atoms thereof,which carbon atoms are joined to and separated by a structure selectedfrom the group consisting of ether linkages and thio ether linkages,dissolving said compound in an alkaline solution, subjecting saidsolution to an oxidizing treatment in the presence of adispersing agentto convert said compound into a polymer in the form of a latex-likedispersion thereoi and separating the polymer from said dispersion inthe form oi" a potentially reactive mass capable 01' being cured byheat.

20. A rubber-like plastic comprising the reaction product 01' anoxidizing agent with a mercaptan compound having one SH group attachedto each of the two terminal carbon atoms of said compound, which carbonatoms are joined the group consistingoi ether linkages and thio 10 etherlinkages, said plastic being capable of being cured by heat.

JOSEPH C. PATRICK.

